Imidazole → (aR)-a-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzeneacetic Acid

HRID 454980노트

반응식

HRID 454980 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2회HCID 11821572Boc-4-hydroxy-D-phenylglycine

생성물 1

HCID 86658147(aR)-a-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzeneacetic Acid수율 123.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (R)-tert Butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid (2.54 g, 9.55 mmol) in DMF (5 mL) was added imidazole (1.43 g, 21 mmol) followed by t-butyldimethylsilyl chloride (1.58 g, 10.5 mmol). The resulting mixture was stirred at rt for overnight. Additional t-butyldimethylsilyl chloride (1.43 g, 9.55 mmol) was added and let the reaction continue for another hour. The reaction mixture was diluted with EtOAc and washed with H2O three times and concentrated. To the residue was added aqueous 1N NaOH and then acidified with concentrated HCl. The resulting mixture was extracted with EtOAc three times. The combined organic layer was dried (MgSO4) and concentrated to provide the titled compound (4.5 g).

후처리

  1. waitcontinue for another hour
  2. washwashed with H2O three times
  3. concentrationconcentrated
  4. additionTo the residue was added aqueous 1N NaOH
  5. extractionThe resulting mixture was extracted with EtOAc three times
  6. dry with materialThe combined organic layer was dried (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2a1287e2a01740aa9b86ce2706ea1673
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497271B2

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